9 painful moments from the Pirates' 20 losing seasons

9 painful moments from the Pirates' 20 losing seasons

With their victory over the Rangers on Monday, the Pittsburgh Pirates won their 82nd game of the 2013 season, ensuring that they will finish over .500 for the first time since 1992. Two decades’ worth of futility make for plenty of lowlights, but the following nine stand out as the most painful of the Pirates’ record 20 consecutive losing seasons. They are, in no particular order:

1. Randall Simon demolishes a sausage

Simon probably thought he was being funny when he took a bat to the top of Guido the Italian Racing sausage’s head in July of 2003, but sausages are no laughing matter in Milwaukee and running in giant sausage costumes is apparently more difficult than it looks. The swing toppled two tubed meats, and earned Simon a three-game suspension and over $2,000’s worth of fines.

2. Losing Jose Bautista — twice

Jose Bautista (PHOTO: AP Photo)

It would have been impossible to expect Bautista to twice lead the league in home runs and make four consecutive All-Star teams, but that probably doesn’t lessen the sting for the Pirates’ organization. Pittsburgh drafted Bautista in 2000, lost him to the Orioles in the Rule 5 draft in 2004, then got him back later that season in a three-team trade. Bautista played regularly for the Pirates from 2006 to 2008, when they traded him to the Blue Jays for catcher Robinzon Diaz. Diaz is not as good as Bautista.

3. Lloyd McClendon steals first base

(PHOTO: Gene J. Puskar/AP Photo)

McClendon managed the Bucs through some of their darkest times, so you can excuse him for taking first base and walking away after arguing with an umpire over a close call at the bag in June, 2001. The base was still in the Pirates’ clubhouse as of 2011.

4. Turner Ward runs through the wall

This is actually a highlight, but it’s too awesome to ignore here. And it speaks to the condition of Three Rivers Stadium before the Pirates moved into beautiful PNC Park. Ward bruised his right arm and suffered cuts from shattered fiberglass on the catch. After the game, he said, “I sure feel like I hit a wall, but I think I’m in better shape than that wall is.”

5. Operation Shutdown

Derek Bell (left) (PHOTO: Mark Duncan/AP Photo)

Bell hit .173 for the Pirates in an injury-plagued 2001 season, but when he got word that he wasn’t inked in to a starting job during spring training of 2002, he threatened to enact “Operation Shutdown.” Unfortunately, the Pirates cut Bell soon after and no one got to find out exactly what Operation Shutdown meant. Great band name, though. Bell never played affiliated ball again.

6. Doug Strange’s 1998

Doug Strange (right) (PHOTO: Pat Sullivan/AP Photo)

It feels mean to pick on Strange, since he’s not the one who gave himself so much playing time during the 1998 season. But Strange got 201 plate appearances that year and hit .173 with a .217 on-base percentage and a .216 slugging. By park- and league-adjusted OPS+, it was the worst offensive season by anyone with more than 200 plate appearances in 27 years.

7. Losing 20-0

(PHOTO: Keith Srakocic/AP Photo)

The Pirates worst season of the last 20 was actually in 2010, right before they started showing signs of getting better. In April of that year, their losing stretch hit its nadir when they lost 20-0 to the Milwaukee Brewers. It remains among the five most lopsided shutouts in Major League history.

8. Drafting failures

Bryan Bullington (PHOTO: Jake Schoellkopf/AP Photo)

Every Major League team has missed plenty of times in drafts, but for a long stretch of time the Pirates did it with particular aplomb. The team’s first picks in 1993, 1994, 1998 and 1999 never played in the Majors. In 2002, they took college pitcher Bryan Bullington first overall in a draft that saw Zack Greinke, Cole Hamels, Matt Cain, Prince Fielder and Nick Swisher go in the first round.

9. Whiffing on Wakefield

The 1992 Pirates (PHOTO: Chaz Palla/AP Photo)

Tim Wakefield emerged as a sensation in the Pirates’ pennant run in 1992. But the knuckleball is fickle and difficult to master, and Wakefield struggled and found himself demoted in 1993. After a rough season toiling for the Pirates’ Class AA club in 1994, Wakefield was released in April of 1995. The Red Sox scooped him up less than a week later. He joined their rotation a month later, and went on to win 186 games for Boston over the next 17 seasons.

In retrospect, it’s hard to blame Lloyd McClendon for taking first base and going home.

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